Potassium Carbonate → HCID 67465242, compound

HRID 2171111Notes

Reaction equation

HRID 2171111 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[C:5]([O:11][CH:12]([F:14])[F:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH:12]([F:13])[F:14])=[C:6]([O:9][CH3:10])[C:7]=1[O:8][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 674670406-Bromo-3-(difluoromethoxy)-2-methoxyphenol

Product 1

HCID 67465242HCID 67465242, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 6-bromo-3-(difluoromethoxy)-2-methoxyphenol (200 mg, 0.743 mmol) in acetonitrile (10 mL) was added potassium carbonate (307 mg, 2.228 mmol) and 1-(bromomethyl)-4-(methylsulfonyl)benzene (368.6 mg, 1.48 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure to afford 300 mg of 1-Bromo-4-(difluoromethoxy)-3-methoxy-2-(4-(methylsulfonyl)benzyloxy)benzene crude product as a solid.

Workup

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-05868ea1ceaa4a2b94acd46021f6f9ae
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…